


A Fistful of Jacksons

by 427-67Impala (australis86)



Category: Supernatural
Genre: Dominant!Sam, Dominant/Top Sam, Established Relationship, M/M, Prostitution, Top!Sam, Wincest - Freeform, bottom!Dean
Language: English
Status: Completed
Published: 2012-01-20
Updated: 2012-01-20
Packaged: 2017-10-29 21:00:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,313
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/324123
Author URL: https://archiveofourown.org/users/australis86/pseuds/427-67Impala
Summary: <blockquote class="userstuff">
              <p>Money is tighter than usual for the Winchesters - hustling pool & poker hasn't paid much lately, and Sam is shocked to find out what his brother has been doing to supplement their income.<br/>Wincest, oneshot. Complete.</p>
            </blockquote>





	A Fistful of Jacksons

**Author's Note:**

> _Word count:_ 4,351  
>  _Setting:_ Mid-season 1
> 
> This fic exists partly because of people's reviews of _Late-Night Laundry_ \- you guys seem to really get off on dominant!Sam!  
>  As for where the rest of it came from... *shrug* ;)

_Redding, California_

Sam didn't like bars, really. He'd much prefer to be sitting in their nice, quiet (and clean) motel room, as opposed to the dive Dean had dragged him to tonight. The place was dim, smelled vaguely of stale beer and cigarette smoke, there were too many power ballads on the jukebox, and the old wooden table he was sitting at wobbled whenever he turned the pages of his newspaper.

While Sam was languishing in the corner wishing he was somewhere else, Dean was holding court at the bar. He was chatting to a few random people, drinking his beloved El Sol, and generally having a pretty good time by the looks of it. Sam hoped he might be asking around about the case that had brought them to town in the first place, but he didn't like his chances.

Dean had been talking to one guy for about five minutes straight - much longer than case-related conversations with the general public usually lasted - and Sam was becoming increasingly sure that the chat was purely social. The guy (who was also drinking El Sol) looked about Dean's age, and they seemed to be getting along famously.

Sam sighed and looked back down at his newspaper. Unlike his brother, Sam was working. Bodies that turn up looking like they've been chewed on by something the size of a mountain lion tend to attract attention, and hence get reported in the local paper.

The reporter that had written this particular article naturally assumed it  _was_  a rogue mountain lion, but he/she had still done their homework on the victims - the story was full of all kinds of interesting facts that might be helpful to an inquisitive hunter. It had led Sam to a couple of theories, but they wouldn't know anything for sure until they visited the medical examiner the following morning. Truth be told, Sam would rather be in the city morgue than in that bar.

Sam finished his article, and his beer, and looked up to try and catch Dean's attention. Instead, he saw his brother disappearing down the hallway that led to the men's room.

_Typical. Looks like I'm going to have to get my own beer._

He folded up his paper and grabbed his empty glass, and was just about to get out of his chair when the well-built guy Dean had been talking to - who Sam was thinking of as Blondie, due to his bleached-blonde dye job - threw a few furtive glances around the room, got up, and followed Dean into the hallway.

That got Sam's attention. Something about the way Blondie had scanned the room tickled his instincts, telling him something odd was going on. Even though he knew it was probably nothing, and he was very sure Dean could look after himself, Sam still found himself bypassing the bar and following the pair of them into the dimly-lit, wood-panelled hall. He was just in time to see the door at the other end swing shut behind Blondie - it wasn't the bathroom door, though. It was a heavy fire door marked 'Exit', and it evidently led outside.

Sam furrowed his brow. It wasn't uncommon for Dean to partake in the odd cigarette, and he'd seen a pack in Blondie's shirt pocket… maybe they'd gone outside for a smoke.

 _Or maybe Blondie went outside on his own._  He checked the men's room, just out of curiosity, but came up empty. Dean was nowhere to be seen.

Sam stood in the hallway for a few seconds, staring at the exit door and chewing on his bottom lip. He couldn't put his finger on it, but something wasn't right about this.

 _If they went outside for a cigarette, why didn't they leave together? Why did Dean go_ first _?_

Sam went the rest of the way down the hallway, and slowly cracked open the fire door. He didn't hear anything, so he opened it further and took a look outside into the night.

The door opened onto a badly-lit, dead-end alleyway that ran between the back of the bar and the building behind it. There was a pile of empty kegs to the right, and a couple of dumpsters to the left, along with all the other miscellaneous junk you find in alleys.

None of that registered in Sam's mind, though. His attention was occupied by what was going on at the very end of the alley.

Blondie had shoved Dean up against the red brick wall, face-first, and was holding him there with a well-muscled forearm across his shoulders. And both Dean and Blondie's jeans were down around their knees.

As Sam watched with wide eyes, absolutely dumbstruck, Dean took a handful of bills Blondie held out to him and handed him a small foil square in return. Dean shoved the cash into his shirt pocket as the other man tore the foil package open and -

_Holy shit._

Intellectually, Sam knew exactly what he was seeing. He just didn't understand  _why_.

Money had been kind of tight lately, but Dean hadn't seemed any more worried about it than usual. The usually-lucrative pool hustling and poker games had been pretty few and far between, but the fake credit cards were still working (mostly), and Dean always seemed to have cash in his wallet…

_Oh._

Suddenly, Sam thought he understood where Dean had been getting that money.

Sam was brought crashing back to Earth by a low groan from the end of the alley. Dean and Blondie had gotten down to business, and Dean was really earning his fee tonight - Blondie was pressing him uncomfortably hard against the wall, left forearm across the eldest Winchester's shoulders, gripping the back of Dean's neck possessively as he repeatedly drove into him. Even from across the alley, Sam could see Blondie wasn't being gentle.

What really struck Sam was that Dean was just  _accepting_  it. He'd braced himself against the wall and was resting his head against his right forearm, eyes shut tight and lips slightly parted. He looked like he was trying to imagine he was somewhere else.

Blondie grabbed him roughly at the hips and pulled back, trying to get a better angle, and Dean started to moan a little. Sam couldn't tell if they were moans of pleasure or pain, but the way Blondie was grasping the back of Dean's neck and pushing him against the bricks, Sam got the impression Dean probably wasn't enjoying it.

He considered intervening and putting a stop to it, but quickly dismissed the idea. He knew Dean wouldn't have wanted him to see this in the first place.

_He wouldn't want his baby brother to know he's turning tricks for gas money._

Sam knew he shouldn't be standing in the doorway watching it happen. It wasn't that he'd never seen this side of Dean - when they were teenagers, before he'd gone away to Stanford, they'd tried having a physical relationship. But it was hard with their father around, so the experiment had only lasted a couple of weeks. Then Sam had gone away to college, and Dean had gone on the road with John...

Lately though, ever since he'd realised he and Dean might be on their own for a while yet, Sam had been thinking about those weeks they'd been together. They'd still been getting to know each other when the experiment ended, and since Dean had come to get him at Stanford there had been times when Sam had almost asked if he wanted to try again.

Now, watching his brother screwing another guy, Sam really wished he'd just bitten the bullet and  _asked_.

Sam went back inside before Dean and Blondie were done, but he didn't go straight into the bar. First, he had to make a quick detour into the men's room to do something about the aching hard-on that Dean's... extra-curricular activities... had inspired.

It didn't take him long. As he stood in the corner stall, leaning back against the tiled wall with his eyes shut and his jeans around his knees, just the  _memory_  of his brother's moans was almost enough. Sam had never been so hard in his life, and it was all over after only a few quick pulls.

By the time Dean came back inside, Sam was sitting nonchalantly at his table in the corner, glass in hand, pretending to read his newspaper as if nothing had happened. He was drinking whiskey now, though - after what he'd seen tonight, beer just wasn't going to cut it.

Sam didn't confront Dean about what he saw in the alley. The best he could bring himself to do was comment on how much fun he looked like he'd been having at the bar, and that earned him a patented Dean Winchester smartass response about how Sam made The Man with No Name look like a social butterfly and, if he didn't spend the whole night sitting the corner, he might even have a little fun himself.

o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o-o- o-o-o

For Sam, the next day seemed to drag on forever - Dean pretending he hadn't fucked a guy for money in the alley the night before, and Sam pretending he hadn't seen him do it.

Honestly, he was surprised at how easily Dean was able to lie about what had really been going on. If he hadn't followed Blondie up that hallway, he would never have known. Dean covered so well it was a little scary.

Sam had come to the conclusion that his brother either really didn't mind screwing random guys for $100 bucks a pop (he knew it was $100, because he'd found five twenty dollar notes in Dean's shirt pocket while he was showering the morning after), or he'd just had plenty of practice at lying about it. Sam's money was on the latter; after seeing the way Blondie had treated his big brother last night, he just couldn't believe Dean would do it unless he had to.

He almost asked Dean the question a few times, actually - while they were alone in the Impala, driving to the ME's office and witnesses' houses, for instance. And he almost choked on his coffee when Dean paid for lunch with one of the twenties he'd earned in the alley.

In the end, Sam couldn't bring himself to do it. Every time he opened his mouth to try, he ran into the same problem: how do you tell your big brother you know he's whoring himself out to keep you both in food and fuel?

Fortunately, though, Sam had come up with another solution.

Predictably, Dean dragged him back to the same bar that night. As Sam sat at his corner table, newspaper open in front of him, he watched an athletic-looking guy about his own age approach Dean at the bar and strike up a conversation - this one was wearing an LA Dodgers baseball cap, so Sam christened him 'Blue'. It only took a couple of minutes for Dean to again head off up the hallway, closely followed by his new, baseball-loving friend.

Sam immediately got up and went after them - once again, Dean had chosen to use the alley - and peered out through the fire door that Blue had left ajar. Dean was standing with his back against the wall, a little smile on his face as he shrugged out of his jacket. They were closer to the door this time, and Sam could hear every word that was said.

"Those are some pretty lips, but that's not what I'm here for," Blue was saying, as he spun Dean around and shoved him up against the alley wall. As with Blondie, he just  _let_  this guy hold him against the bricks.

"It's your money, man." Dean didn't seem worried - evidently, blowjobs were for cheapskates.

Sam slipped quietly out into the alley and crept up behind them. He wasn't worried about sneaking up on Blue - when they first arrived at the bar earlier that night, he'd gone outside to take a fictional phone call from Bobby, allegedly about the monster they were hunting. It was at that point he'd put his plan into action and made a financial arrangement of his own with the good-looking guy wearing a Dodgers baseball cap.

The youngest Winchester came to a stop beside Blue and handed him a $50 note - his fee for luring Dean outside into the alley. The guy took it, giving Sam a nod, and quickly and quietly headed out of the alley and into the street - he'd done exactly what the big guy with the cash had asked, but now he had his money he didn't want to stick around and see what happened next. Judging by the ruse that Sasquatch had told him to use, Blue had a pretty good idea where things were headed.

Now that they were alone Sam stepped up behind Dean and planted a hand between his shoulder blades, keeping him hard up against the wall.

"Not so fast, buddy. Dead presidents first." Dean held up a hand, and Sam silently gave him his last two fifties. He stayed directly behind Dean, right up against his back, and held the folded bills in the end of his fingers, but he shouldn't have worried - Dean didn't even try to turn his head and make eye contact. As far as he was concerned, it was still Blue standing behind him.

Dean shoved the cash deep into the front pocket of his jeans, and his hand came out holding a foil-wrapped condom. He passed it back to Sam, who took it wordlessly and, after a second's pause, tore it open with his teeth. He didn't want to release his grip and risk Dean turning around and freaking out when he saw who his john actually was.

When he'd thought this scheme up earlier that day, Sam intended for this to be the point where he put an end to the charade. But, as he stood there in the alley with an open condom in his hand and his big brother pressed against the wall and unzipping his jeans, Sam hesitated.

He didn't  _want_  to stop here. He wanted to go through with it, holding Dean hard up against this old, graffiti-covered brick wall, in the dark alley behind the bar. He wanted to take his brother like he'd seen that random guy do the night before, when Dean had just  _let_  him.

But if he went all the way… Sam couldn't be sure how Dean would react to that.

If he stopped right now and Dean didn't appreciate the joke, there was no harm done. An awkward conversation, maybe, but nothing too serious. But if he got his $100-worth out of Dean and it turned out he  _didn't_  want to start screwing his little brother again… that would be it. They'd be done. There wasn't going to be anything he could do to fix it.

Sam was just about to open his mouth and tell Dean what was going on, but was interrupted by him reaching a hand around behind his body and unsnapping the button on Sam's jeans.

It was only then that he noticed Dean wasn't pressed hard up against the wall anymore. He was leaning back into Sam, his back pressing against his baby brother's chest. Sam stopped pushing him away and let his hand just rest on his brother's shoulder, suddenly a little unsure what to do next.

"Don't say anything. I know it's you."

Those words took Sam's breath away. He hadn't expected Dean to work it out so quickly, but that wasn't what sent his heart rate through the roof. It wasn't even Dean's tone of voice - lower and more sensual now; like he was talking to a lover, not a customer.

It was that, even now he knew it was Sam,  _Dean wanted to keep going_.

Sam didn't argue. His heart suddenly pounding, he unzipped his jeans and yanked them and his boxer shorts down far enough to free his achingly hard cock. Dean let out a pleased little gasp as he felt the heat of Sam's hard-on press against the skin of his bare ass, and couldn't help but push his hips back a little to grind against his brother's body.

Sam closed his eyes and let his head drop back as he groaned, just taking a second to savour the sensation. Dean, however, was sick of waiting - he spat into the palm of his right hand, reached back and used his own saliva to lubricate the not-inconsiderable length of Sam's cock.

Before he knew he was doing it, Sam had slapped Dean's hand away and shoved him roughly back up against the wall with a little growl. "It's my money, remember?" he breathed, close to Dean's ear.

Dean didn't reply - he let Sam hold him there, his cheek pressed hard against the red bricks, smiling the whole time. If he'd been able to turn around (Sam was much stronger than he remembered) he would've seen a little smile on Sam's lips too. The youngest Winchester was enjoying being in charge.

His left hand still planted firmly on Dean's left shoulder blade and his right hand gripping his hip hard enough to leave bruises, Sam slowly and deliberately rubbed the head of his cock up and down between Dean's ass cheeks a few times.

Dean whined impatiently - actually  _whined_  - and tried to push his hips back to get Sam inside. Sam's iron grip defeated him, though, and he actually heard a breathy little laugh from his baby brother. He was enjoying the chance to tease the older Winchester.

Dean decided to let Sammy have his fun. He relaxed under his brother's grip, and felt Sam ease off a little. Dean took a long breath as he felt that hot hardness touch him again, gentler this time, and Sam's thumb stroking his hip as he found the right spot and the pressure increased...

Despite his original intention of treating Dean like the whore he evidently was, Sam tried to be gentle. He shouldn't have worried - instead of the strained moan of pain he expected from his big brother, Sam got a groan of  _pleasure_  as he slid inside.

Sam thought briefly that it probably made sense. Dean wasn't new at this, apparently, and of  _course_ he'd done a little preparation before they went out. He didn't dwell on it, though - the only thing he could think about was the tight heat of Dean's body pressing in around him, hips pushing back against him in time with his own thrusts… And God, those little grunts and groans falling from Dean's lips were driving him  _mad_ …

Sam didn't loosen his grip on Dean as he thrust into him. He knew Dean was going to be sore tomorrow, and that he was holding on so tight that he was leaving bruises on his hips (and shoulders, and upper arms), but he didn't let up and Dean didn't stop him.

Dean didn't  _want_  to stop him. His improvised lubrication had long since evaporated, he could feel Sam's nails digging into the trapezius muscle above his left collarbone, and he had to push back against his thrusts so his own hard-on wasn't scraped red-raw by the brick wall, but Dean didn't care.

He didn't care that this alley was a public place. He didn't care that he was going to feel this for  _days_. His little brother had found out he was selling his body for gas money, and he didn't mind. In fact, Dean was pretty sure what Sam was doing now was the exact  _opposite_  of minding.

When Sam eventually came, both boys were breathing hard and covered in a thin sheen of sweat. Sam released his grip and left Dean leaning up against the wall, literally weak at the knees, and panting just as hard as his little brother.

As he stepped back and did up his jeans, Sam took a second to admire Dean's bare ass before the eldest Winchester, oblivious to Sam's admiration of his backside, slowly (and carefully) pulled up his jeans and slipped back into his jacket with a little sigh. Fully dressed again, Dean turned slowly to face his baby brother.

"You set me up." Dean couldn't quite bring himself to look him in the eye.

Sam sighed. "Would you prefer I'd brought it up over lunch?"

Dean shrugged. He couldn't blame Sam - there was probably no _good_  way to start this conversation.

"So how long have you known?" he asked, running a hand back through his hair with a self-conscious expression on his face that confirmed what Sam had surmised - he didn't  _like_ selling his body for money. Or that his little brother knew he was doing it, for that matter.

"Since yesterday."

A quick look of surprise flashed across Dean's face, and he couldn't keep it out of his voice. "What took you so long?"

Sam winced.  _Obviously, he's been at this for quite a while._

Dean noticed his baby brother cringe and paused before he went on, trying to find the right words. "Sam, I only do it when I've got no other choice. There's been pretty slim pickings at pool and poker and stuff lately, and…" Dean trailed off, with another shrug. He still wasn't meeting Sam's gaze.

Sam studied Dean as he spoke. His big brother obviously wasn't proud of what he'd been doing, and Sam didn't want to push him on it. This wasn't the time or the place for an in-depth chick-flick moment like that. He wasn't going to let Dean get away with it forever - there were a  _lot_  of questions Sam wanted answers to - but that was a can of worms to be opened at a later date.

"Okay," he said, and a look of relief washed over Dean's face. He had been sure Sam was going to want to have it out here and now.

"But you're never doing it again."

That got a weary sigh in response. Sam could just imagine what the next words out of Dean's mouth were going to be -  _"We've got to eat, Sam, and the Impala needs gas…"_  - but he wasn't quite done yet.

"No boyfriend of mine is going to be turning tricks on the side."

Dean looked sharply up at Sam, his face a picture of confusion. He opened his mouth to reply, but immediately closed it again.

"We tried it once, remember?" Sam reminded him, and Dean nodded cautiously. He had to admit, those few weeks with Sam - alone, before their Dad got back - had been some of the best weeks of his life.

Even just now, when they'd been having a semi-anonymous quickie in a dirty alley behind a random bar in a random town, it felt  _right_  with Sam. And it would be  _so_  good to be in a relationship where he didn't have to keep secrets…

"And besides, you deserve better than sex in alleys with strangers that treat you like Blondie did last night," Sam continued, frowning slightly as he remembered the tense, pained look on Dean's face as he'd just stood there and taken it. "When I saw Blondie having his way with you, I realised something - I don't want other guys to  _touch_  you. I want you all to myself."

Dean winced as he imagined Sam watching that, unconsciously stretching his back. His encounters with Blondie and Sam had lasted just over half an hour in total, but being bent over like that for so long was hell on his lower back.

"You okay?" Sam asked, concerned, but Dean just chuckled.

"I'm awesome. Actually, that was the best sex I've had in months."

Sam couldn't help but smile at that. "So do we have a deal, then?"

Dean smiled. It was a lazy, sated little smile that Sam recognised from all the times his brother had slipped back into their motel room after a one-night-stand.

"Yeah, we've got a deal," he replied, and pulled Sam in close for a kiss.

The way his baby brother's lean, pliant body moulded itself against Dean's removed any lingering doubts - this was how it was supposed to be. Sam wouldn't ever try force him into anything he didn't want, he'd never grab the back of Dean's neck like he was a dog, and the only bruises he'd ever leave would be ones Dean had asked for. He'd rather Sam hadn't seen other guys do it, either, but there was nothing he could do about that now.

When they finally came up for air, the first thing Dean did was hand Sam his $100 back.

"I'm not going to take your money, Sam. But after what you just did, I think it's only fair you buy me a drink," Dean told him, simply, and a grin slowly spread across Sam's face.

"Most people  _start_ these things that way, you know," the eldest Winchester continued, smiling as he turned his back on Sam and started towards the fire door.

_Well, you should know...!_

Sam didn't say it out loud, though - he valued his life too much to risk it by teasing his big brother just now.

"And don't think you'll get away with pulling that macho dominant crap again," Dean added, looking pointedly back over his shoulder at Sam. He couldn't help it - Sam had to laugh at that.

"And what makes you think  _you're_  going to be in charge?" he asked, eyebrows raised.

"Because I'm older, Sammy," Dean replied matter-of-factly, like that should be enough of a reason in and of itself.

Sam looked at him witheringly, but Dean just laughed as he opened the fire door and went back inside. Sam followed silently, a little smile still on his lips - he didn't care if Dean got the last word or not. Sam already had the only thing he really wanted.

**Author's Note:**

> I don't know where this stuff comes from, I swear. ;)
> 
> I have no idea how you guys are going to react to the idea of Dean selling his body for food/fuel money, so I want you to tell me. Whether it's a couple of sentences or a short essay, I'm interested to know what you guys think. And, if you enjoyed it, hit the 'share' button and tell someone!


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